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SML0089

Sigma-Aldrich

Abacavir sulfate

≥98% (HPLC)

Synonym(s):

(1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol sulfate, ABC, Abacavir Hemisulfate

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About This Item

Empirical Formula (Hill Notation):
C14H18N6O · 0.5 H2SO4
CAS Number:
188062-50-2
Molecular Weight:
335.37
MDL number:
MFCD04112763
UNSPSC Code:
12352200
PubChem Substance ID:
329825149
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -30 to -40°, c = 0.5 in methanol

color

white to tan

solubility

H2O: ≥17 mg/mL

originator

GlaxoSmithKline

storage temp.

2-8°C

SMILES string

OS(O)(=O)=O.Nc1nc(NC2CC2)c3ncn([C@@H]4C[C@H](CO)C=C4)c3n1.Nc5nc(NC6CC6)c7ncn([C@@H]8C[C@H](CO)C=C8)c7n5

InChI

1S/2C14H18N6O.H2O4S/c2*15-14-18-12(17-9-2-3-9)11-13(19-14)20(7-16-11)10-4-1-8(5-10)6-21;1-5(2,3)4/h2*1,4,7-10,21H,2-3,5-6H2,(H3,15,17,18,19);(H2,1,2,3,4)/t2*8-,10+;/m11./s1

InChI key

WMHSRBZIJNQHKT-FFKFEZPRSA-N

General description

Abacavir exhibits antiviral activity. It is associated with myocardial infarction and fatal hypersensitivity reaction (HSR).

Application

Abacavir sulfate has been used as a compound to validate the P19C5 gastrulation in mouse. It has also been used to induces chromosomal double-strand breaks (DSBs) and kills adult T cell leukemia (ATL) cells.
Abacavir sulfate has been used in the cytotoxicity to test its tumour promoting activity U937 cells.

Biochem/physiol Actions

Abacavir incorporated in the cells is converted to triphosphate containing guanine analog carbovir (CBV) and it favors the generation of higher double stranded breaks (DSBs).
Abacavir sulfate is a Nucleoside analog reverse transcriptase inhibitor (NRTI); guanosine analog used to treat HIV and AIDS.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H317,H319,H341,H351,H361

Hazard Classifications

Carc. 2 - Eye Irrit. 2 - Muta. 2 - Repr. 2 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tumour Promoting Potentials of HAART backbone (NNRTIs and NRTIs) leading to increase cancer risk among AIDs patients
Aisha Z
Microbioz Journals,Journal of Microbiology and Biomedical Research, 4(3), e1400203-e1400203 (2018)
Hypersensitivity reaction associated with abacavir therapy in an Indian HIV patient-A case report
Janardhanan M, et al.
Journal of Clinical and Diagnostic Research : JCDR, 8(9), HD01-HD01 (2014)
Abacavir use and risk for myocardial infarction and cardiovascular events: pooled analysis of data from clinical trials
Nan C, et al.
Open forum infectious diseases, 5(5), ofy086-ofy086 (2018)
Abacavir, an anti-HIV-1 drug, targets TDP1-deficient adult T cell leukemia
Tada K, et al.
Science advances, 1(3), e1400203-e1400203 (2015)
Boe-Hyun Kim et al.
Viruses, 16(5) (2024-05-25)
EcoHIV is a chimeric HIV that replicates in mice in CD4+ T cells, macrophages, and microglia (but not in neurons), causing lasting neurocognitive impairment resembling neurocognitive disease in people living with HIV. The present study was designed to develop EcoHIV-susceptible
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